Synthesis, characterization and crystal structures of (Z)-1-(triarylstannyl)-3-phenyl-1-buten-3-ols and their arylhalostannyl derivatives

Article abstract of DOI:10.1016/j.poly.2003.09.012

(Z)-1-(tri-o-tolylstannyl)-3-phenyl-1-buten-3-ol (1) and (Z)-1-(tri-p-tolylstannyl)-3-phenyl-1-buten-3-ol (2) were synthesized by the additive reaction of 3-phenyl-1-butyn-3-ol with tri-o-tolyltin and tri-p-tolyltin hydrides. One of the aryl groups in compounds 1 and 2 was substituted by Cl, Br, I to yield derivatives of the type PhC(CH ₃)(OH)CH=CHSn(aryl)₂X [aryl=o-tolyl, X = Cl (3); aryl = p-tolyl, X = Cl (4); aryl = o-tolyl, X = Br (5); aryl = p-tolyl, X = Br (6); aryl = o-tolyl, X = I (7); aryl = p-tolyl, X = I (8)]. Compounds 1-8 were characterized by elemental analysis, ¹H NMR and FT-IR spectroscopy. The crystal structures of 1, 2 and 5 have been determined by single crystal X-ray diffraction analysis. The Sn atom in 1 and 2 exhibits tetrahedral geometry distorted towards trigonal bipyramidal due to a weak intramolecular interaction between Sn and the hydroxyl O atoms [2.879(5) and 2.859(4) ?], while the Sn atom in 5 adopts a trigonal bipyramidal geometry with a significant Sn(1) ← O interaction [2.483(4) ?].

Full text of DOI:10.1016/j.poly.2003.09.012

Polyhedron 22 (2003) 3523–3527
www.elsevier.com/locate/poly
Synthesis, characterization and crystal structures of
(Z)-1-(triarylstannyl)-3-phenyl-1-buten-3-ols and their
arylhalostannyl derivatives
a,b
Dong-Sheng Zhu , Ze-Min Mei , Chun-Sheng Lu , Wei Gao , Yue-Tao Zhang ,
a
a
a
a
€
a,c,
a
Ying Mu *, Zong-Mu Wang
a
School of Chemistry, Jilin University, Changchun 130023, PR China
School of Chemistry, Northeast Normal University, Changchun 130024, PR China
Key Laboratory for Supramolecular Structure and Materials of the Ministry of Education, Jilin University, Changchun 130023, PR China
b
c
Received 15 July 2003; accepted 19 September 2003
Abstract
(Z)-1-(tri-o-tolylstannyl)-3-phenyl-1-buten-3-ol (1) and (Z)-1-(tri-p-tolylstannyl)-3-phenyl-1-buten-3-ol (2) were synthesized by
the additive reaction of 3-phenyl-1-butyn-3-ol with tri-o-tolyltin and tri-p-tolyltin hydride. One of the aryl groups in compounds
1 and 2 was substituted by Cl, Br, I to yield derivatives of the type PhC(CH3)(OH)CH@CHSn(aryl)2X [aryl ¼ o-tolyl, X ¼ Cl
(3); aryl ¼ p-tolyl, X ¼ Cl (4); aryl ¼ o-tolyl, X ¼ Br (5); aryl ¼ p-tolyl, X ¼ Br (6); aryl ¼ o-tolyl, X ¼ I (7); aryl ¼ p-tolyl, X ¼ I
1
(8)]. Compounds 1–8 were characterized by elemental analysis, H NMR and FT-IR spectroscopy. The crystal structures of 1, 2
and 5 have been determined by single crystal X-ray diffraction analysis. The Sn atom in 1 and 2 exhibits tetrahedral geometry
distorted towards trigonal bipyramidal due to a weak intramolecular interaction between Sn and the hydroxyl O atoms
ꢀ
[2.879(5) and 2.859(4) A], while the Sn atom in 5 adopts a trigonal bipyramidal geometry with a significant Sn(1) O in-
ꢀ
teraction [2.483(4) A].
Ó 2003 Elsevier Ltd. All rights reserved.
Keywords: Organotin compounds; Aryltin compounds; FT-IR spectroscopy; NMR spectroscopy; X-ray crystal structure
1. Introduction
located in a distorted tetrahedral environment, while
the Sn atom adopts a trigonal bipyramidal geometry
in the diarylhalostannyl and aryldihalostannyl deriva-
tives of the type (Z)–(Ar3 ꢀ nXnSn)–CH@CH–C(OH)
RR0 due to strong HO ! Sn interaction. It has been
reported that the antitumor activity of these com-
pounds is related to the strength of the HO ! Sn
interaction, which is determined by the number and
nature of the aryl groups and the Lewis acidity of the
central tin atom [5,11,12]. In this paper, the synthesis
and structure of (Z)-1-(triarylstannyl)-3-phenyl-1-bu-
ten-3-ols (aryl ¼ o-tolyl and p-tolyl) and their aryl-
halostannyl derivatives are reported. Their structural
features, particularly the HO ! Sn coordination in-
teraction, are discussed. These compounds are likely
to serve as new models for further investigation on the
structure-antitumor activity relationship.
Since Crowe et al. [1] reported the antitumour ac-
tivity and hypotoxicity of organotin compounds, great
attention has been paid to the synthesis, structure and
antitumour activity of such compounds. In particular,
compounds of the type (Z)–(Ar3Sn)–CH@CH–C(OH)
RR0 (Ar ¼ phenyl and p-tolyl) and their arylhalostan-
nyl derivatives have been actively studied [2–12]. The
solid-state structures of (Z)–(Ar3Sn)–CH@CH–C(OH)
RR0 exhibit a weak intramolecular HO ! Sn interac-
tion. As a result, the Sn atom in these compounds is
* Corresponding author. Tel.: +804318499136; fax: +864318949334.
E-mail address: ymu@mail.jlu.edu.cn (Y. Mu).
0277-5387/$ - see front matter Ó 2003 Elsevier Ltd. All rights reserved.
doi:10.1016/j.poly.2003.09.012

3524
D.-S. Zhu et al. / Polyhedron 22 (2003) 3523–3527
2. Experimental
(d, JHH ¼ 12.6 Hz, CH–Sn); 7.07 (d, JHH ¼ 12.6 Hz, CH);
7.58 (d, JHH ¼ 7.2 Hz, o-H, Ph); 7.10–7.32 (m, m- + p-H,
Ph); 2.27 (s, CH3, Ph–CH3); 1.52 (s, CH3). Anal. Calc.
for C31H32OSn: C, 69.04; H, 5.98; Sn, 22.20. Found: C,
68.95; H, 5.88; Sn, 22.09%.
2.1. Reagents and general techniques
Elemental analyses were carried out on a Perkin–El-
mer PE 2400 CHN instrument and gravimetric analysis
was carried out for Sn. H NMR spectra were recorded
1
2.2.2.2. (Z)-1-(tri-p-tolylstannyl)-3-phenyl-1-buten-3-ol
(2). Yield: 72%; m.p. (recrystallized from ethanol):
97.2–98.0 °C. IR (KBr pellets): mCO 1066 cmꢀ1, mOH: 3550
in CDCl3 on a Varian Mercury 300 MHz spectrometer.
Infrared spectra (KBr pellets) were recorded on an Alpha
Centauri FI/IR spectrometer (400–4000 cmꢀ1 range).
Hypnone, tri-o-tolyltin chloride, tri-p-tolyltin chlo-
ride, LiAlH4, iodine monochloride, bromine and iodine
were obtained from commercial sources and used
without further purification. 3-Phenyl-1-butyn-3-ol was
prepared by a modified literature method [13]. Tri-o-
tolyltin and tri-p-tolyltin hydrides were obtained from
reaction of tri-o-tolyltin chloride and tri-p-tolyltin
chloride with LiAlH4 in dried diethyl ether [14,15]. Di-
ethyl ether was dried and distilled from Na–K alloy
under nitrogen. Other solvents were used without puri-
fication.
1
cmꢀ1. H NMR (CDCl3, ppm): d 1.76 (s, OH); 6.23 (d,
JHH ¼ 12.6 Hz, CH–Sn); 7.05 (d, JHH ¼ 12.6 Hz, 1H,
CH); 7.50 (d, JHH ¼ 7.8 Hz, o-H, Ph); 7.15–7.31 (m, m-
+ p-H, Ph); 2.34 (s, CH3, Ph–CH3); 1.61 (s, CH3). Anal.
Calc. for C31H32OSn: C, 69.04; H, 5.97; Sn, 22.20.
Found: C, 68.92; H, 5.85; Sn, 22.19%.
2.2.2.3. (Z)-1-(chlorodi-o-tolylstannyl)-3-phenyl-1-bu-
ten-3-ol (3). Yield: 63%; m.p. (recrystallized from cy-
clohexane): 136.8–137.7 °C. IR (KBr pellets): mCO 1060
cmꢀ1, mOH 3390 cmꢀ1. 1H NMR (CDCl3, ppm): d 2.69 (s,
OH); 6.40 (d, JHH ¼ 10.2 Hz, CH–Sn); 6.86 (d,
JHH ¼ 10.2 Hz, CH); 7.49, 7.61 (d, JHH ¼ 6.7 Hz, o-H,
Ph); 7.08–7.40 (m, m- + p-H, Ph); 2.55 (s, CH3, Ph–
CH3); 1.68 (s, CH3). Anal. Calc. for C24H25ClOSn: C,
59.60; H, 5.21; Sn, 24.55. Found: C, 59.62; H, 5.30; Sn,
24.60%.
2.2. Synthesis
2.2.1. Synthesis of compounds 1 and 2
3-Phenyl-1-butyn-3-ol (14.62 g, 100 mmol) and dib-
enzoyl peroxide (100 mg) were added to a solution of tri-
o-tolyltin hydride in diethyl ether prepared from the
reaction of tri-o-tolyltin chloride (53.44 g, 125 mmol)
with LiAlH4 (4.74 g, 125 mmol). The mixture was stirred
for 30 h at room temperature under nitrogen and the
solvent was evaporated off. The residue was recrystal-
lized from ethanol to yield 45.30 g of 1 as a white
crystalline solid.
The same procedure was used for the reaction of 3-
phenyl-1-butyn-3-ol with tri-p-tolyltin hydride. Single
crystals of both compounds suitable for X-ray analysis
were obtained by slow evaporation of an ethanol solu-
tion at room temperature over one week.
2.2.2.4. (Z)-1-(chlorodi-p-tolylstannyl)-3-phenyl-1-bu-
ten-3-ol (4). Yield: 71%; m.p. (recrystallized from cy-
clohexane): 133.6–134.8 °C. IR (KBr pellets): mCO 1055
1
cmꢀ1, mOH 3383 cmꢀ1. H NMR (CDCl3, ppm): d: 2.70
(s, OH); 6.38 (d, JHH ¼ 9.8 Hz, CH–Sn); 6.83 (d,
JHH ¼ 9.8 Hz, CH); 7.48 (d, JHH ¼ 6.5 Hz, o-H, Ph);
7.04–7.39 (m, m- + p-H, Ph); 2.56 (s, CH3, Ph–CH3);
1.75 (s, CH3). Anal. Calc. for C24H25ClOSn: C, 59.60; H,
5.21; Sn, 24.55. Found: C, 59.63; H, 5.29; Sn, 24.65%.
2.2.2.5. (Z)-1-(bromodi-o-tolylstannyl)-3-phenyl-1-bu-
ten-3-ol (5). Yield: 71%; m.p. (recrystallized from cy-
clohexane): 135.3–136.1 °C. IR (KBr pellets): mCO 1060
cmꢀ1, mOH 3400 cmꢀ1. 1H NMR (CDCl3, ppm): d 2.48 (s,
OH); 6.48 (d, JHH ¼ 11.4 Hz, CH–Sn); 6.92 (d,
JHH ¼ 11.4 Hz, CH); 7.51 (d, JHH ¼ 6.9 Hz, o-H, Ph);
7.03–7.37 (m, m- + p-H, Ph); 2.54 (s, CH3, Ph–CH3);
1.64 (s, CH3). Anal. Calc. for C24H25BrOSn: C, 54.59; H,
4.77; Sn, 22.48. Found: C, 54.49; H, 4.81; Sn, 22.58%.
2.2.2. Reaction of compounds 1 and 2 with halogens
Bromine (160 mg, 1 mmol) in 15 ml of CCl4 was
added slowly with stirring to a solution of 1 (539 mg, 1
mmol) in 20 ml of CCl4 at )5 °C. The color of bromine
disappeared immediately. The mixture was allowed to
warm to room temperature and stirred for 1 h. The
solvent was evaporated off and the residue was recrys-
tallized from cyclohexane to give 375 mg of compound 5
as white crystals.
2.2.2.6. (Z)-1-(bromodi-p-tolylstannyl)-3-phenyl-1-bu-
ten-3-ol (6). Yield: 77%; m.p. (recrystallized from cy-
clohexane): 126.4–127.5 °C. IR (KBr pellets): mCO 1060
cmꢀ1, mOH 3392 cmꢀ1. 1H NMR (CDCl3, ppm): d 2.52 (s,
OH); 6.50 (d, JHH ¼ 11.2 Hz, CH–Sn); 6.94 (d,
JHH ¼ 11.2 Hz, CH); 7.51 (d, JHH ¼ 6.8 Hz, o-H, Ph);
7.05–7.40 (m, m- + p-H, Ph); 2.55 (s, CH3, Ph–CH3);
1.68 (s, CH3). Anal. Calc. for C24H25BrOSn: C, 54.59; H,
4.77; Sn, 22.48. Found: C, 54.50; H, 4.71; Sn, 22.53%.
The other vinyl-o-tolyltin and vinyl-p-tolyltin halides
were prepared analogously using ICl or I2.
2.2.2.1. (Z)-1-(tri-o-tolylstannyl)-3-phenyl-1-buten-3-ol
(1). Yield: 85%; m.p. (recrystallized from ethanol):
126.6–127.7 °C. IR (KBr pellets): mCO 1068 cmꢀ1, mOH
3552 cmꢀ1. 1H NMR (CDCl3, ppm): d 1.54 (s, OH); 6.28

D.-S. Zhu et al. / Polyhedron 22 (2003) 3523–3527
3525
2.2.2.7. (Z)-1-(iododi-o-tolylstannyl)-3-phenyl-1-buten-
3-ol (7). Yield: 85%; m.p. (recrystallized from cyclo-
hexane): 145.2–145.9 °C. IR (KBr pellets): mCO 1070
cmꢀ1, mOH 3405 cmꢀ1. 1H NMR (CDCl3, ppm): d 2.38 (s,
OH); 6.53 (d, JHH ¼ 11.7 Hz, CH–Sn); 6.80 (d,
JHH ¼ 11.7 Hz, CH); 7.49 (d, JHH ¼ 7.2 Hz, o-H, Ph);
7.04–7.36 (m, m- + p-H, Ph); 2.53 (s, CH3, Ph–CH3);
1.62 (s, CH3). Anal. Calc. for C24H25IOSn: C, 50.13; H,
4.38; Sn, 20.64. Found: C, 50.08; H, 4.31; Sn, 20.77%.
hydrogen atoms were generated geometrically. The pa-
rameters of data collection and structure refinement are
given in Table 1.
3. Results and discussion
3.1. Synthesis
Compounds 1–8 were synthesized according to
Scheme 1. Reactions of compounds 1 and 2 with halo-
gens in a 1:1 molar ratio yield the corresponding
monohalides 3, 4, 5, 6, 7 and 8, respectively. Com-
pounds 1–8 were all characterized by IR, H NMR and
elemental analysis.
2.2.2.8. (Z)-1-(iododi-p-tolylstannyl)-3-phenyl-1-buten-
3-ol (8). Yield: 81%; m.p. (recrystallized from cyclo-
hexane):140.2–141.5 °C. IR (KBr pellets): mCO 1065
1
1
cmꢀ1, mOH: 3398 cmꢀ1. H NMR (CDCl3, ppm): d 2.39
(s, OH); 6.55 (d, JHH ¼ 11.5 Hz, CH–Sn); 6.89 (d,
JHH ¼ 11.5 Hz, CH); 7.52 (d, JHH ¼ 7.2 Hz, o-H, Ph); (m,
m- + p-H, Ph); 2.52 (s, CH3, Ph–CH3); 1.64 (s, CH3).
Anal. Calc. for C24H25IOSn: C, 50.13; H, 4.38; Sn, 20.64.
Found: C, 50.11; H, 4.45; Sn, 20.76%.
1
3.2. H NMR and IR spectra
The solution 1H NMR spectra of compounds 1–8 are
consistent with their structures. All spectra show char-
acteristic ethylenic proton signals of a doublet of dou-
2.3. X-ray crystallography
3
blets with JðHC@CHÞ ¼ 9.8–12.6 Hz in the regions of
3
Diffraction data for compounds 1, 2 and 5 were col-
lected on a Siemens P4 diffractometer with graphite
6.27–6.57 and 6.80–7.07 ppm. The JðHC@CHÞ coupling
constant of 12.6 Hz observed for 1 and 2 is quite large
since the cis coupling constant in similar compounds
with a five-membered ring substituent usually amounts
to 8 Hz or even less [17]. In regard to the stannyl
ꢀ
monochromated Mo Ka radiation (k ¼ 0:71073 A) at
ambient temperature. The structures were solved by the
heavy-atom method (SHELXS 97), and were refined by
full-matrix least squares techniques (SHELXL 97) [16].
Non-hydrogen atoms were refined anisotropically. The
3
group, the JðHC@CHÞ coupling constant decreases in the
order Sn(aryl)3 > Sn(aryl)2I > Sn(aryl)2Br > Sn(aryl)Cl,
Table 1
Crystal data and details of structure refinement parameters for compounds 1, 2 and 5
Compound
1
2
5
Formula
C31H32OSn
539.26
293(2)
C31H32OSn
539.26
293(2)
C24H25BrOSn
528.04
293(2)
Molecular weight
Temperature (K)
Crystal size (mm)
0.52 ꢁ 0.44 ꢁ 0.32
0.71073
triclinic
0.52 ꢁ 0.40 ꢁ 0.32
0.71073
0.50 ꢁ 0.46 ꢁ 0.32
0.71073
ꢀ
Wavelength (A)
Crystal system
Space group
Cell constants
monoclinic
P21=n
monoclinic
P21=c
ꢁ
P1
ꢀ
a (A)
10.5044(19)
11.298(3)
11.9927(18)
68.932(14)
86.898(13)
86.343(17)
1324.7(4)
2
11.428(3)
18.840(4)
13.0874(16)
17.879(2)
7.5287(13)
16.636(3)
ꢀ
b (A)
ꢀ
c (A)
a (°)
b (°)
c (°)
108.384(13)
92.071(14)
3
ꢀ
V (A )
2674.0(9)
4
2237.8(6)
4
Z
Dcalc: (g cmꢀ3
F ð000Þ
)
1.352
552
1.340
1104
x
52.00
0.975
1.567
1048
x
52.02
2.938
Scan mode
2hmax
x
52.02
0.984
Absorption coefficient
l(Mo Ka) (mmꢀ1
)
R1 (on F for reflections with
I > 2rðIÞ)
0.0498 (for 4189 reflections)
0.0344 (for 3423 reflections)
0.0434 (for 2849 reflections)
wR2 (on F 2 for all reflections)
Goodness-of-fit
0.1332 (for 5071 reflections)
1.046
0.0713 (for 5249 reflections)
0.833
0.1004 (for 4405 reflections)
0.900

3526
D.-S. Zhu et al. / Polyhedron 22 (2003) 3523–3527
Fig. 2. The molecular structure and crystallographic numbering
scheme for compound 2.
vinyl residue, adopts a distorted tetrahedral geometry
with C–Sn–C angles ranging from 103.37(19)° to
115.78(19)°. The C(1)–Sn(1)–C(11) angle (115.78(19)°) is
significantly larger than other C–Sn–C angles due to
weak coordination of the O(1) atom of the cyclopenta-
nol hydroxyl group. The distance between the O(1) and
Scheme 1.
ꢀ
Sn(1) atoms is 2.879(5) A, which is significantly less than
ꢀ
the sum of their van der Waals radii [3.70 A] [18]). The
weak coordination of the O(1) atom also influences the
strength of the Sn(1)–C(o-tolyl) bond. As a result,
Sn(o-tolyl)3 > Sn(p-tolyl)3 and Sn(o-tolyl)2X > Sn(p-
tolyl)2X. The chemical shifts of OH shift to high field
following the same order, which indicates that the
strength of the HO ! Sn interaction increases with the
decrease in the steric hindrance of the stannyl group.
The infrared spectra of all compounds 1–8 show the
presence of strong absorptions in the regions of 1055–
1070 and 3398–3552 cmꢀ1, which can be assigned to
ꢀ
Sn(1)–C(21) is longer by 0.03 A than the other two
Sn(1)–C(o-tolyl) bonds. The fact that the Z isomer ra-
ther than the E isomer was obtained from this type of
reaction [2] might be attributed to the weak intramo-
lecular O ! Sn coordination. The geometry about the
Sn atom in 2 is essentially the same as that for 1 with the
C–Sn–C angles ranging from 102.91(14)° to 116.67(14)°.
m
and m
stretching vibrations, respectively.
ðC–OÞ
ðO–HÞ
3.3. Description of compounds 1, 2 and 5
The molecular structures of compounds 1, 2 and 5 are
given in Figs. 1–3, respectively. The Sn atom in 1,
bonded to three o-tolyl groups and the C(1) atom of the
Fig. 1. The molecular structure and crystallographic numbering
scheme for compound 1.
Fig. 3. The molecular structure and crystallographic numbering
scheme for compound 5.

D.-S. Zhu et al. / Polyhedron 22 (2003) 3523–3527
3527
The C(1)–Sn(1)–C(31) angle of 116.67(14)° is much
wider than the corresponding angle in 1 due to stronger
interaction between the O(1) atom and the Sn atom in 2,
which can be clearly seen from the relatively short
obtained free of charge from The Director, CCDC 12
Union Road, Cambridge CB2 1EZ, UK (fax: +44-1223-
336033; e-mail: deposit@ccdc.cam.ac.uk or www: http://
www.ccdc.cam.ac.uk).
ꢀ
Sn ꢂ ꢂ ꢂ O(1) distance (2.859(4) A). These results also re-
flect greater Lewis acidity of the Sn atom in 2 than in 1.
The Sn atom in 5 is five coordinated and the molecule
has a distorted trigonal bipyramid geometry with the
trigonal plane defined by C(1), C(11) and C(21) atoms
and the axial positions occupied by the Br(1) and O(1)
atoms, which is similar to a reported analogue (Z)-1-[2-
(chlorodi-p-tolylstannyl)vinyl]-1-cycloheptanol [11]. The
Acknowledgements
This work was supported by the National Natural
Science Foundation of China (Nos. 29734143 and
29672013).
ꢀ
Sn ꢂ ꢂ ꢂ O(1) distance of 2.483(4) A is in the range of a
normal Sn–O coordination bond length [2,8,11], indi-
cating that the Sn atom in 5 is formally coordinated by
the O(1) atom of the hydroxyl group and the Lewis
acidity of the Sn atom in the (o-tolyl)2SnBr moiety is
greater than in the (o-tolyl)3Sn moiety. On the other
References
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ꢀ
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4. Conclusions
We have synthesized and characterized (Z)-1-(tria-
rylstannyl)-3-phenyl-1-buten-3-ol (aryl ¼ o-tolyl, p-tolyl)
and several monohalide derivatives. (Z)-1-(triarylstan-
nyl)-3-phenyl-1-buten-3-ol adopts a distorted tetrahe-
dral geometry, while the Sn atom in the monohalide
derivatives is located inside a trigonal bipyramid.
[11] F. Fu, H. Li, D. Zhu, Q. Fang, H. Pan, E.R.T. Tiekink, F.
Kayser, M. Biesemans, I. Verbruggen, R. Willem, M. Gielen, J.
Organomet. Chem. 490 (1995) 163.
[12] H.C. Dai, Q.H. Ying, X.H. Wang, S.M. Yue, H.D. Pan, X. Chen,
Polyhedron 17 (1998) 2503.
[13] H.D. Vercruijsse, W. De Graaf, L. Brandsma, Synth. Commun.
18 (1988) 131.
[14] H.D. Kuivila, O.F. Beumel Jr., J. Am. Chem. Soc. 83 (1961) 1246.
[15] D.H. Lorenz, P. Shapiro, A. Stern, E.I. Becker, J. Org. Chem. 28
(1964) 2335.
5. Supplementary material
ꢂ
[16] G.M. Sheldrick, SHELX97 and SHELX97, University of Gottingen,
Crystallographic data for the structural analysis have
been deposited with the Cambridge Crystallographic
Data Centre, CCDC No. 210842 for compound 1,
CCDC No. 210843 for compound 2, CCDC No. 210844
for compound 5. Copies of this information may be
ꢂ
Gottingen, Germany, 1997.
[17] R.M. Silverstein, C.G. Bassler, T.C. Morrill, Spectrometric
Identification of Organic Compounds, 4th ed., Wiley, New York,
1981, p. 235.
[18] A. Bondi, J. Phys. Chem. 68 (1964) 441.